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Isle of Wight

$99+ Cheap flights from Westchester County to Isle of Wight, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — RIC
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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Cheap flight deals from Westchester County to Isle of Wight

Keep the following information in mind while searching for Westchester County to Isle of Wight flight deals. Data was last updated January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$195
(Kiwi.com)

One-way from

$99
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$199
Provider with most accurate pricing for New York (NYC)-Norfolk flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Norfolk flights.
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From Westchester County to Isle of Wight
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One-way flight from Westchester County to Isle of Wight
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Highest demand for flights based on searches. 4% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Westchester County to Isle of Wight

Cheapest flights from Westchester County to Isle of Wight
Explore the most affordable flight options available from Westchester County to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/512:08 pm
HPN
-
ORF
1 stop4h 42m
Breeze Airways
Sun 2/81:09 pm
ORF
-
HPN
1 stop7h 21m
Breeze Airways
Deal found 1/14$195
This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/308:00 am
HPN
-
ORF
2 stops24h 00m
Breeze Airways
Sun 2/11:09 pm
ORF
-
HPN
1 stop7h 21m
Breeze Airways
Deal found 1/14$207
This American Airlines deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/155:30 pm
HPN
-
ORF
1 stop5h 32m
American Airlines
Sat 2/216:15 am
ORF
-
HPN
1 stop4h 43m
American Airlines
Deal found 1/15$211
This American Airlines deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/127:47 am
HPN
-
ORF
1 stop6h 29m
American Airlines
Thu 2/1910:45 am
ORF
-
HPN
1 stop3h 45m
American Airlines
Deal found 1/13$233
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/16:40 pm
HPN
-
ORF
1 stop4h 30m
American Airlines
Sun 2/83:06 pm
ORF
-
HPN
1 stop5h 02m
American Airlines
Deal found 1/14$234
This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/298:00 am
HPN
-
ORF
1 stop14h 04m
Multiple Airlines
Mon 2/26:45 am
ORF
-
HPN
2 stops28h 43m
Multiple Airlines
Deal found 1/14$246
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/291:30 pm
HPN
-
ORF
1 stop5h 11m
American Airlines
Mon 2/26:00 am
ORF
-
HPN
1 stop3h 29m
American Airlines
Deal found 1/14$249
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/281:17 pm
HPN
-
ORF
2 stops32h 33m
Multiple Airlines
Sun 2/11:09 pm
ORF
-
HPN
1 stop7h 21m
Multiple Airlines
Deal found 1/13$253
This American Airlines deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/211:00 am
HPN
-
ORF
1 stop5h 10m
American Airlines
Tue 2/1011:07 am
ORF
-
HPN
1 stop3h 32m
American Airlines
Deal found 1/13$254
This American Airlines deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:54 pm
HPN
-
ORF
1 stop5h 05m
American Airlines
Tue 3/175:18 pm
ORF
-
HPN
1 stop5h 41m
American Airlines
Deal found 1/15$255
This American Airlines deal was found by Cheapflights users on 1/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/126:30 am
HPN
-
ORF
1 stop3h 34m
American Airlines
Sun 2/226:14 am
ORF
-
HPN
1 stop4h 44m
American Airlines
Deal found 1/15$263

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Isle of Wight that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
Use the filters below to find and compare flights from Westchester County to Isle of Wight that are best for you.

Fly from

Westchester County

Fly to

Isle of Wight

Route

Depart

Return

Price

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 2/5

12:08 pm-4:50 pm

1 stop4h 42m

Norfolk

Sun 2/8

1:09 pm-8:30 pm

1 stop7h 21m

$195

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Fri 1/30

8:00 am-8:00 am

2 stops24h 00m

Norfolk

Sun 2/1

1:09 pm-8:30 pm

1 stop7h 21m

$207

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sun 2/15

5:30 pm-11:02 pm

1 stop5h 32m

Norfolk

Sat 2/21

6:15 am-10:58 am

1 stop4h 43m

$211

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 2/12

7:47 am-2:16 pm

1 stop6h 29m

Norfolk

Thu 2/19

10:45 am-2:30 pm

1 stop3h 45m

$233

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sun 2/1

6:40 pm-11:10 pm

1 stop4h 30m

Norfolk

Sun 2/8

3:06 pm-8:08 pm

1 stop5h 02m

$234

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 1/29

8:00 am-10:04 pm

1 stop14h 04m

Norfolk

Mon 2/2

6:45 am-11:28 am

2 stops28h 43m

$246

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Thu 1/29

1:30 pm-6:41 pm

1 stop5h 11m

Norfolk

Mon 2/2

6:00 am-9:29 am

1 stop3h 29m

$249

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Sat 1/31

11:00 am-4:10 pm

1 stop5h 10m

Norfolk

Wed 2/4

6:00 am-9:29 am

1 stop3h 29m

$249

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Fri 1/30

5:15 pm-11:05 pm

1 stop5h 50m

Norfolk

Sun 2/1

6:00 am-9:29 am

1 stop3h 29m

$249

White PlainsNorfolk

HPN - ORF

HPNORF

White Plains Westchester County

Mon 2/2

11:00 am-4:10 pm

1 stop5h 10m

Norfolk

Tue 2/10

11:07 am-2:39 pm

1 stop3h 32m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 22 results
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Best time to book a flight from Westchester County to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from Westchester County with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Westchester County to Isle of Wight

What is the cheapest month to book a flight from Westchester County to Isle of Wight?

Currently, February is the cheapest month in which you can book a flight from Westchester County to Isle of Wight (average of $182). Flying from Westchester County to Isle of Wight in December is currently the most expensive (average of $861). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Isle of Wight

Get insights into the airlines that provide service to Isle of Wight. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Isle of Wight. Reviews last updated January 15, 2026.
Peruse reviews from past customers who have flown with American Airlines from Westchester County to Isle of Wight to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,136 reviews

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,136 reviews
American Airlines
7.2
Good
11,136 reviews

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Isle of Wight. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Westchester County to Isle of Wight?

    Airlines like Breeze Airways and American Airlines fly from Westchester County to Isle of Wight in about 4h 42m. The time it takes to get you to your destination can typically vary by up to 50m. Westchester County and Isle of Wight are separated by a distance of 318 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Westchester County to Isle of Wight that include hotel bookings?

    Yes. In addition to deals on Westchester County to Isle of Wight flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Isle of Wight?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Westchester County to Isle of Wight.

  • Can I find deals for business class flights from Westchester County to Isle of Wight?

    Yes. Cheapflights offers flight deals from Westchester County to Isle of Wight by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Westchester County to Isle of Wight?

    Currently, February is the cheapest month in which you can book a flight from Westchester County to Isle of Wight (average of $182). Flying from Westchester County to Isle of Wight in December is currently the most expensive (average of $861). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Westchester County to Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Westchester County to Isle of Wight

Discover the top airline that operate flights from Westchester County to Isle of Wight. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$452FlexibilityNo cancel feeOn-time71%

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